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13 Life and Finance Lessons I Learned in My First Year of Self-Employment

Stefanie Addis
5 min readJun 16, 2020

Before resigning from a solid and secure banking career, I had a paycheck I could count on that took care of all of our expenses and then enough to put towards retirement. I was also stubborn and set in my ways; thinking all choices I had made thus far were the best.

And, even though I had created spreadsheets of our expected expenses and how to live off of savings while getting my business up and running, you better believe unexpected expenses came up that would annihilate our financial planning.

So without further ado, here are 13 lessons I learned, and hopefully you can glean some helpful advice from it:

1.Unexpected expenses WILL happen-guaranteed. And-they won’t be small!

Within a month of being unemployed, our water heater went out. We had to replace it — which was not cheap and was not something we had counted on.

About 2 months after that, our kitchen faucet completely broke and we had to buy one and have it installed-as I don’t know how to do it myself.

2. Health insurance costs suck when you are paying full price yourself

At first, I kept Cobra because I didn’t want to start over with all new doctors. And let me tell you-wow Cobra coverage is disgustingly expensive.

Eventually, I had to replace it with Marketplace insurance is horribly subpar, and still not cheap if you don’t qualify for discounts. I didn’t qualify for discounts as I wasn’t making income yet- so I was still paying close to $500 a month just for myself.

To make it worse, the agent I used could not find any providers that covered my preferred health network or hospital. I was not prepared for that. I always had great health insurance and could go to my health care network that I had been going to for about 20 years. That network doesn’t accept ANY marketplace plans at all whatsoever-so that is a major negative.

3. On the topic of health insurance-health emergencies WILL & CAN happen unexpectedly.

About 6 months after being unemployed and still not on my feet yet with income-I had a severe leg injury which led to blood clots in my lungs and throughout my leg. I was in the ICU for 3 days and it was very serious.

Without thinking- I went to the hospital that I have always gone to- as they are the BEST! Well, guess what- not in-network. I didn’t care though- I was in the ER and couldn’t breathe or walk, so I wasn’t about to go try to find another hospital.

The bill was astronomical! I’m still on a payment plan for it.

4. I really didn’t need to buy name brand groceries for all items. Generic is just as good in many cases and has a positive impact on your grocery budget each month.

5. I learned to control my impulse spending, not only on groceries, but online and in person.

6. Cable is overrated. We now use streaming services like Pluto for free, as well as Sling and Netflix for other channels. Yes, it took some getting used to but now I would never switch back.

7. Wants are not the same as needs-financially. Yes, I wanted to get a newer car but no I didn’t need it. It would cause my car insurance to go up and I would have another loan.

No thanks.

Before this life change though-I wouldn’t have batted an eye.

8. After reviewing my expenses and spending closely, I don’t need to spend nearly as much as I was before. Now I know where every penny goes and I spend so much less. If you really analyze your spending with a budget, you will find ways to cut costs and you can spend less than what you make each month.

9. Walmart for groceries-just as good as Kroger! I use the pickup and they always pick great produce for us. I’ve never had an issue with their food.

It’s super convenient and as I mentioned above-it completely cut out my impulse shopping. No-I don’t need that fancy lavender mustard that is at my eye level that I wasn’t expecting. And no, I don’t need the bourbon-glazed pecans that are next to the healthy raw almonds.

Now that I don’t go inside when shopping, I don’t see those tantalizing and tempting goodies.

10. Libraries are your best friend if you’re a book junkie.

I came to realize that I don’t need to buy a hardcover book every time I want to read a new book. How many have I purchased that I ended up not even liking? And then I would take them over to Half Price Books for a few dollars?

I’m not keen on eReaders, so I still opt for the turning of paper pages. Aaaah it’s my favorite. But now, I just reserve them online and go get them from my local library.

I have come across a few books that I fell in love with (I read nonfiction so a lot are reference and self-improvement) so I make it a point to go buy them. I always check eBay first though.

I mean-they just sit in my bookshelf anyway, why did I need a brand new hardback book each time? SMH-Lesson learned.

11. Having a well-funded emergency fund is VITAL. If I hadn’t been building it up for 2 years I would have been in serious trouble. Plus, Covid-19 hit during this time so if I hadn’t been prepared financially and was out there working for a company, I could have lost my job and been in dire circumstances.

12. I learned to NEVER value myself based on my job title-ever again.

Life is more than that, and for close to 20 years I became my job and stopped living life.

Now, I make it a point to get the sleep I need, to exercise like I need to, and to get out to the park several times a week with my husband for some much-needed nature and decompressing.
I make it a point to see my family more often- not just on holidays. For goodness sake, we live in the same city; there’s no excuse for that crappy behavior.

13. Having a few close friends (even if they don’t live in the same city) is priceless. I had lost contact with all friends in my circle, and thankfully I’ve been able to reconnect.

Working from home is extremely lonely, sometimes to the point it hurts-so connect with them and cherish those friendships-because you’re gonna need them.

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Stefanie Addis

Freelance writer and wooden spoon survivor. Personal finance and wellness blogger at www.wellnessinablender.com.